JP5704922B2 - Sunflower oil with high heat stability - Google Patents
Sunflower oil with high heat stability Download PDFInfo
- Publication number
- JP5704922B2 JP5704922B2 JP2010538804A JP2010538804A JP5704922B2 JP 5704922 B2 JP5704922 B2 JP 5704922B2 JP 2010538804 A JP2010538804 A JP 2010538804A JP 2010538804 A JP2010538804 A JP 2010538804A JP 5704922 B2 JP5704922 B2 JP 5704922B2
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- JP
- Japan
- Prior art keywords
- oil
- tocopherol
- content
- sunflower
- seeds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 235000019486 Sunflower oil Nutrition 0.000 title claims description 53
- 239000002600 sunflower oil Substances 0.000 title claims description 53
- 239000003921 oil Substances 0.000 claims description 167
- 235000019198 oils Nutrition 0.000 claims description 167
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 101
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 95
- 229930195729 fatty acid Natural products 0.000 claims description 95
- 239000000194 fatty acid Substances 0.000 claims description 95
- 150000004665 fatty acids Chemical class 0.000 claims description 95
- 229930003799 tocopherol Natural products 0.000 claims description 92
- 239000011732 tocopherol Substances 0.000 claims description 92
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 83
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 79
- 235000010384 tocopherol Nutrition 0.000 claims description 75
- 229960001295 tocopherol Drugs 0.000 claims description 75
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 claims description 54
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 48
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 48
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 48
- 239000005642 Oleic acid Substances 0.000 claims description 48
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 48
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 48
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 48
- 241000196324 Embryophyta Species 0.000 claims description 46
- 235000021314 Palmitic acid Nutrition 0.000 claims description 41
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 41
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 35
- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 33
- 239000002478 γ-tocopherol Substances 0.000 claims description 33
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims description 31
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 claims description 27
- 235000010389 delta-tocopherol Nutrition 0.000 claims description 27
- 239000002446 δ-tocopherol Substances 0.000 claims description 27
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 25
- 241000208818 Helianthus Species 0.000 claims description 24
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 24
- 235000021355 Stearic acid Nutrition 0.000 claims description 21
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 21
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 21
- 239000008117 stearic acid Substances 0.000 claims description 21
- 235000019149 tocopherols Nutrition 0.000 claims description 17
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 17
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 16
- 235000020238 sunflower seed Nutrition 0.000 claims description 16
- 235000004835 α-tocopherol Nutrition 0.000 claims description 15
- 239000002076 α-tocopherol Substances 0.000 claims description 15
- 229940087168 alpha tocopherol Drugs 0.000 claims description 14
- 229960000984 tocofersolan Drugs 0.000 claims description 14
- 235000013305 food Nutrition 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 12
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 12
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 12
- 235000020778 linoleic acid Nutrition 0.000 claims description 12
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 12
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 10
- 230000006698 induction Effects 0.000 claims description 7
- 230000010165 autogamy Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000002551 biofuel Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 description 44
- 238000009826 distribution Methods 0.000 description 31
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 230000003078 antioxidant effect Effects 0.000 description 13
- 235000015112 vegetable and seed oil Nutrition 0.000 description 12
- 235000007680 β-tocopherol Nutrition 0.000 description 8
- 239000011590 β-tocopherol Substances 0.000 description 8
- 230000002068 genetic effect Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- 229940066595 beta tocopherol Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000010525 oxidative degradation reaction Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical group O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000002640 tocopherol group Chemical group 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 125000001020 α-tocopherol group Chemical group 0.000 description 2
- WGVKWNUPNGFDFJ-UHFFFAOYSA-N β-tocopherol group Chemical group CC1(OC2=C(C=C(C(=C2CC1)C)O)C)CCCC(CCCC(CCCC(C)C)C)C WGVKWNUPNGFDFJ-UHFFFAOYSA-N 0.000 description 2
- 125000003810 γ-tocopherol group Chemical group 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 238000011993 High Performance Size Exclusion Chromatography Methods 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004186 co-expression Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000009402 cross-breeding Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000005017 genetic modification Effects 0.000 description 1
- 230000007614 genetic variation Effects 0.000 description 1
- 235000013617 genetically modified food Nutrition 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 1
- 238000003976 plant breeding Methods 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000008117 seed development Effects 0.000 description 1
- 230000035040 seed growth Effects 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/10—Seeds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
- A01H6/14—Asteraceae or Compositae, e.g. safflower, sunflower, artichoke or lettuce
- A01H6/1464—Helianthus annuus [sunflower]
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1014—Biomass of vegetal origin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Physiology (AREA)
- Environmental Sciences (AREA)
- Food Science & Technology (AREA)
- Developmental Biology & Embryology (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
- Fodder In General (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Description
本発明は農業分野、食品分野および工業分野に属するものである。本発明の対象とするヒマワリ油は現在、存在している他のヒマワリ油よりも非常に高い熱安定性を有する。本発明のヒマワリ油は、高い熱安定性により、食品分野(揚げ物)および工業分野(バイオ潤滑油、バイオ燃料)の両分野において、高温が必要なまたは発生する家庭内処理および工業的処理に適している。 The present invention belongs to the agricultural field, food field and industrial field. The sunflower oil targeted by the present invention has a much higher thermal stability than other sunflower oils presently present. The sunflower oil of the present invention is suitable for in-house and industrial treatments that require or generate high temperatures in both the food (fried) and industrial (bio-lubricating oil, biofuel) fields due to their high thermal stability. ing.
植物油は高温が必要なまたは発生する処理に使用されるため、当該植物油は高い熱安定性または熱安定度を有することが要求される。植物油は、食品調理(揚げ調理、焼き調理)または摩擦処理(動力装置および機械装置への注油)の一般的な高温条件に供されると、酸化、重合、加水分解、環化および異性化などの一連の油分解過程が起こり、結果として不愉快なにおいや風味のある生成物や栄養の点で好ましくない特性を示す生成物が形成される(非特許文献1)。油の熱安定性が高いほど、油分解過程の発生は少なくなるので、当該油の有効寿命は長くなる。 Since vegetable oils are used in processes that require or generate high temperatures, the vegetable oils are required to have high thermal stability or thermal stability. Vegetable oil is subject to oxidation, polymerization, hydrolysis, cyclization, isomerization, etc. when subjected to the general high temperature conditions of food cooking (fried cooking, grilling) or friction treatment (lubricating power and machinery) As a result, an unpleasant odor and flavor product and a product exhibiting undesirable characteristics in terms of nutrition are formed (Non-Patent Document 1). The higher the thermal stability of the oil, the less the oil cracking process occurs and the longer the useful life of the oil.
植物油の熱安定性は主に、当該油の不飽和度および当該油中の抗酸化特性を有する物質の存在によって決まる。当該抗酸化特性を有する物質は、加熱時に油を保護し、分解過程の発生を遅らせる。油の不飽和度は脂肪酸分布によって決定される。脂肪酸は、その炭化水素鎖の不飽和度または二重結合の数が増えるほど、酸化に対する感受性がより強くなる。植物油における最も一般的な脂肪酸のうち、リノレン酸(多不飽和で3個の二重結合を有する)が酸化に対して最も感受性が強く、次いで、リノール酸(多不飽和で2個の二重結合を有する)、オレイン酸(モノ不飽和で1個の二重結合を有する)、およびステアリン酸およびパルミチン酸(飽和で二重結合を含まない)の順で続く(非特許文献2)。 The thermal stability of vegetable oils is mainly determined by the degree of unsaturation of the oil and the presence of substances with antioxidant properties in the oil. Substances with such antioxidant properties protect the oil when heated and delay the onset of the degradation process. The degree of unsaturation of the oil is determined by the fatty acid distribution. Fatty acids become more susceptible to oxidation as the degree of unsaturation of the hydrocarbon chain or the number of double bonds increases. Of the most common fatty acids in vegetable oils, linolenic acid (polyunsaturated and has 3 double bonds) is most sensitive to oxidation, followed by linoleic acid (polyunsaturated and 2 doubles) Followed by oleic acid (monounsaturated and having one double bond), and stearic acid and palmitic acid (saturated and free of double bonds) (Non-Patent Document 2).
脂肪種子は抗酸化特性を有する物質を自然に産生し、中でもトコフェロールが傑出している。トコフェロールはクロマノール基およびフィチル側鎖からなる分子である。トコフェロールには天然に生じる4種類の形態が存在し、アルファ−、ベータ−、ガンマ−、およびデルタ−トコフェロールと呼ばれ、クロマノール環におけるメチル(Me)基の数および位置が互いに異なっている(図1)。 Oilseed naturally produces substances with antioxidant properties, above all tocopherol is outstanding. Tocopherol is a molecule consisting of a chromanol group and a phytyl side chain. There are four naturally occurring forms of tocopherol, called alpha-, beta-, gamma-, and delta-tocopherol, which differ from each other in the number and position of methyl (Me) groups in the chromanol ring (Fig. 1).
トコフェロールは脂溶性物質であるため、脂肪種子中に存在するトコフェロールは抽出処理中、油の方に移行する。ここで、トコフェロールは二重の抗酸化作用を示す。一方で、トコフェロールはインビトロ作用を示す。すなわちトコフェロールは、当該トコフェロールを含有する油と製品(調理された食品)または当該油から誘導される製品(バイオ燃料、バイオ潤滑油)を貯蔵時および使用時において酸化から保護する。他方で、トコフェロールは重要なインビボ抗酸化効果、すなわち生存細胞内での抗酸化効果を発揮する生理活性化合物である。このインビボ抗酸化活性はビタミンE活性として知られている(非特許文献3)。4種類のトコフェロールの間にはそれらのインビトロおよびインビボ抗酸化活性の関係において非常に大きな差がある。このため、アルファ−トコフェロールは、インビボ抗酸化剤またはビタミンEとして最高の有効性を有することで特徴付けられるが、そのインビトロ活性は他のトコフェロールと比較して低い。ポングラッツ等(非特許文献3)は、対照としてアルファ−トコフェロールの抗酸化活性を100%とすることにより、インビボ抗酸化剤としての相対的な有効性を、ベータ−トコフェロールは50%、ガンマ−トコフェロールは25%、デルタ−トコフェロールは1%と測定した。その一方、インビトロ抗酸化剤としての相対的な有効性は、ベータ−トコフェロールが182%、デルタ−トコフェロールが194%、ガンマ−トコフェロールが285%であった。 Since tocopherol is a fat-soluble substance, the tocopherol present in the oil seed is transferred to the oil during the extraction process. Here, tocopherol exhibits a double antioxidant effect. On the other hand, tocopherol exhibits in vitro action. That is, tocopherol protects the tocopherol-containing oil and product (cooked food) or product derived from the oil (biofuel, biolubricant) from oxidation during storage and use. On the other hand, tocopherol is a bioactive compound that exerts an important in vivo antioxidant effect, ie an antioxidant effect in living cells. This in vivo antioxidant activity is known as vitamin E activity (Non-patent Document 3). There are very large differences between the four types of tocopherols in relation to their in vitro and in vivo antioxidant activity. For this reason, alpha-tocopherol is characterized by having the highest efficacy as an in vivo antioxidant or vitamin E, but its in vitro activity is low compared to other tocopherols. Pongrats et al. (Non-Patent Document 3) showed the relative effectiveness as an in vivo antioxidant by setting the antioxidant activity of alpha-tocopherol as 100% as a control, beta-tocopherol being 50%, and gamma-tocopherol. Was 25% and delta-tocopherol was 1%. On the other hand, the relative effectiveness as an in vitro antioxidant was 182% for beta-tocopherol, 194% for delta-tocopherol and 285% for gamma-tocopherol.
天然のヒマワリ油は、パルミチン酸(全脂肪酸の4〜8%)、ステアリン酸(全脂肪酸の2〜6%)、オレイン酸(全脂肪酸の20〜45%)およびリノール酸(全脂肪酸の45〜70%)からなる脂肪酸分布を示す。オレイン酸およびリノール酸の相対的な比率は可変であり、種子の発育時の温度に大きく依存する(非特許文献4)。改良された脂肪酸分布を示す幅広いヒマワリ系統(sunflower lines)が遺伝子改良によって開発されている。開発された主な系統およびそれらの脂肪酸分布を表1に示す。 Natural sunflower oil is composed of palmitic acid (4-8% of total fatty acids), stearic acid (2-6% of total fatty acids), oleic acid (20-45% of total fatty acids) and linoleic acid (45% of total fatty acids). 70%). The relative ratio of oleic acid and linoleic acid is variable and largely depends on the temperature during seed development (Non-patent Document 4). A wide range of sunflower lines with improved fatty acid distribution have been developed by genetic modification. Table 1 shows the main lines developed and their fatty acid distribution.
116:0=パルミチン酸; 18:0=ステアリン酸; 16:1=パルミトレイン酸
18:1 =オレイン酸; 18:2=リノール酸
2寒冷環境下および温暖環境下でそれぞれ得られた標準的ヒマワリのデータ
3著者によって提供されたものではないデータ
1 16: 0 = palmitic acid; 18: 0 = stearic acid; 16: 1 = palmitoleic acid 18: 1 = oleic acid; 18: 2 = linoleic acid
Data Standard sunflower respectively obtained under 2 cold environment and warm environment
Data not provided by 3 authors
天然のヒマワリ油は、全トコフェロールの90%よりも多いアルファ−トコフェロールと、全トコフェロールの5%未満であるベータ−、ガンマ−、およびデルタトコフェロールからなるトコフェロール分布を有することによって特徴付けられる(非特許文献6)。ベータ−トコフェロール含量が高い(全トコフェロールの50%よりも多い)ヒマワリ系統、ガンマ−トコフェロール含量が高い(全トコフェロールの90%よりも多い)ヒマワリ系統、およびデルタ−トコフェロール含量が高い(全トコフェロールの65%よりも多い)ヒマワリ系統は遺伝子改良により開発されている(非特許文献5)。 Natural sunflower oil is characterized by having a tocopherol distribution consisting of more than 90% alpha-tocopherol of total tocopherol and beta-, gamma-, and delta tocopherol that is less than 5% of total tocopherol (non-patented). Reference 6). Sunflower lines with high beta-tocopherol content (greater than 50% of total tocopherols), sunflower lines with high gamma-tocopherol content (greater than 90% of total tocopherols), and high delta-tocopherol content (65% of total tocopherols) Sunflower lines (more than%) have been developed by genetic improvement (Non-Patent Document 5).
主に飽和脂肪酸(ステアリン酸およびパルミチン酸)およびモノ不飽和脂肪酸(オレイン酸)からなる不飽和度の低いヒマワリ油は、不飽和度がより高い標準的なヒマワリ油よりも大きな熱安定性を示す(特許文献1)。さらに、アルファ−トコフェロールが、インビトロ抗酸化力がより高い他のトコフェロール、主にガンマ−およびデルタ−トコフェロールで部分的に置き換えられたヒマワリ油は、アルファ−トコフェロール含量が高い標準的なヒマワリ油よりも大きな熱安定性を示す(特許文献2)。飽和脂肪酸とモノ不飽和脂肪酸との含量によって決定される不飽和度が低く、かつトコフェロール分布におけるアルファ−トコフェロール含量が低い油を種子が産生するヒマワリ植物は現在までのところ開発されていない。 Low degree of unsaturation sunflower oil, consisting mainly of saturated fatty acids (stearic acid and palmitic acid) and monounsaturated fatty acids (oleic acid), exhibits greater thermal stability than standard sunflower oil with higher degree of unsaturation (Patent Document 1). In addition, sunflower oil in which alpha-tocopherol has been partially replaced by other tocopherols that have higher in vitro antioxidant capacity, primarily gamma- and delta-tocopherol, than standard sunflower oil with a high alpha-tocopherol content. Shows great thermal stability (Patent Document 2). No sunflower plant has so far been developed in which seeds produce oils with a low degree of unsaturation as determined by the content of saturated and monounsaturated fatty acids and a low alpha-tocopherol content in the tocopherol distribution.
本発明は、今まで開発された他のヒマワリ油と比較して大きい熱安定性をもたらす脂肪酸分布およびトコフェロール分布に関する一連の特性を有するヒマワリ種子から抽出されるヒマワリ油に関する。 The present invention relates to sunflower oil extracted from sunflower seeds having a range of properties relating to fatty acid distribution and tocopherol distribution that provide greater thermal stability compared to other sunflower oils developed so far.
本発明の対象とするヒマワリ油は、飽和脂肪酸(パルミチン酸およびステアリン酸)含量が該油中に存在する全脂肪酸の15〜45%であり、オレイン酸含量が全脂肪酸の45〜75%であることを特徴とする。当該油はまた、主として主要な飽和脂肪酸がパルミチン酸のときのほとんどの場合は、全脂肪酸の5%よりも多くのパルミトレイン酸も含有し得る。リノール酸の含量は該油中に存在する全脂肪酸の10%未満であり、好ましくは5%未満である。さらにガンマ−およびデルタ−トコフェロールの合計含量は該油中に存在する全トコフェロールの85%よりも多く、アルファ−トコフェロールの含量は全トコフェロールの15%未満であり、全トコフェロールの当該油における含量は油1kgあたり500mg〜1250mg、または1250mgよりも多い。 The sunflower oil targeted by the present invention has a saturated fatty acid (palmitic acid and stearic acid) content of 15-45% of the total fatty acids present in the oil and an oleic acid content of 45-75% of the total fatty acids. It is characterized by that. The oil may also contain more than 5% palmitoleic acid, mainly in most cases when the main saturated fatty acid is palmitic acid. The linoleic acid content is less than 10%, preferably less than 5% of the total fatty acids present in the oil. Furthermore, the total content of gamma- and delta-tocopherol is greater than 85% of the total tocopherol present in the oil, the content of alpha-tocopherol is less than 15% of the total tocopherol, and the total tocopherol content in the oil is More than 500 mg to 1250 mg, or 1250 mg per kg.
本発明のヒマワリ油は、未精製油における温度110℃での10時間の誘導期の後、ランシマット型743装置(Rancimat model 743 apparatus)(メトローム社製(Metrohm AG)、ヘリザウ、スイス国)で測定された油安定性指数が35時間〜120時間、または120時間よりも長い、熱安定性の高い油である。 The sunflower oil of the present invention is measured with a Rancimat model 743 apparatus (Metrohm AG, Helisau, Switzerland) after an induction period of 10 hours at 110 ° C. in unrefined oil. Is a highly heat-stable oil having an oil stability index of 35 hours to 120 hours or longer than 120 hours.
本発明は、上記した特性を有する油を含有するヒマワリの種子、および上記した特性を有する種子を自花受精により産生するヒマワリ植物にも関する。本発明の対象とする種子中において達成されるような脂肪酸およびトコフェロール分布の組み合わせの特性を有する油を産生するヒマワリの種子は現在、存在していない。 The present invention also relates to sunflower seeds containing oils having the above-mentioned characteristics, and sunflower plants that produce seeds having the above-mentioned characteristics by self-fertilization. There are currently no sunflower seeds that produce oils with the combined characteristics of fatty acid and tocopherol distribution as achieved in the seeds of interest of the present invention.
本発明の別の対象は、ヒトおよび動物の食物のために、およびバイオ潤滑油およびバイオ燃料の製造のために、上記油を使用することである。 Another subject of the present invention is the use of said oils for human and animal food and for the production of bio-lubricating oils and biofuels.
本発明は、ヘリアンサス・アニュース・エル種(Helianthus annuus L. species)の植物により産生される種子から抽出されたヒマワリ油に関するものであり、当該植物は、非常に優れた熱安定性をもたらす脂肪酸分布およびトコフェロール分布の特性を有する特別な油を産生する。 The present invention relates to sunflower oil extracted from seeds produced by a plant of Helianthus annuus L. species, which is a fatty acid that provides very good thermal stability. Produces special oils with distribution and tocopherol distribution characteristics.
上記油は、飽和脂肪酸としてのパルミチン酸およびステアリン酸の含量が高く(当該油中の全脂肪酸の15〜45%)、オレイン酸の含量が高く(全脂肪酸の45〜75%)、およびガンマ−およびデルタ−トコフェロールの合計含量が高い(当該油中に存在する全トコフェロールの85%よりも多い)ことを特徴とする。これらの3つの特性の組み合わせによって、当該油に高い熱安定性が付与される。 The oil has a high content of palmitic acid and stearic acid as saturated fatty acids (15-45% of the total fatty acids in the oil), a high content of oleic acid (45-75% of the total fatty acids), and gamma- And a high total content of delta-tocopherol (greater than 85% of the total tocopherol present in the oil). A combination of these three properties imparts high thermal stability to the oil.
当該油はまた、当該油中に存在する全脂肪酸の10%未満、好ましくは5%未満のリノール酸に加えて、主要な飽和脂肪酸がパルミチン酸のときのほとんどの場合は、全脂肪酸の5%よりも多いパルミトレイン酸を含有し得る。 The oil also contains less than 10% of the total fatty acids present in the oil, preferably less than 5% linoleic acid, in most cases 5% of the total fatty acids when the main saturated fatty acid is palmitic acid. May contain more palmitoleic acid.
本発明の1つの実施態様において、パルミトレイン酸含量は当該油中の全脂肪酸の10%よりも多い。 In one embodiment of the invention, the palmitoleic acid content is greater than 10% of the total fatty acids in the oil.
油における最高の油安定性は飽和脂肪酸によってもたらされる。しかしながら、油中のこれら脂肪酸の含量が非常に高いと、揚げ物食品における低い煙点および低い油の栄養価をもたらす。オレイン酸は油に、飽和脂肪酸よりも低い油安定性を付与するが、より高い煙点およびより高い栄養価を付与する。ガンマ−およびデルタ−トコフェロールは、ベータ−およびアルファ−トコフェロールよりも、大きな油安定性を油に付与する。 The best oil stability in the oil is provided by saturated fatty acids. However, a very high content of these fatty acids in the oil results in a low smoke point and low oil nutritional value in the fried food. Oleic acid gives the oil less oil stability than saturated fatty acids, but gives a higher smoke point and higher nutritional value. Gamma- and delta-tocopherol imparts greater oil stability to the oil than beta- and alpha-tocopherol.
本発明の油中のアルファ−トコフェロール含量は当該油中に存在する全トコフェロールの15%未満である。全トコフェロール含量は油1kgあたり500mg〜1250mg、または1250mgよりも多くし得る。 The alpha-tocopherol content in the oil of the present invention is less than 15% of the total tocopherol present in the oil. The total tocopherol content can be 500 mg to 1250 mg per kg of oil, or more than 1250 mg.
当該油は、ヒマワリにおいて既に従来から開発されている以下の個々の特徴を組み換えることにより得られた:
a)飽和脂肪酸含量が高いこと。種子の油中、脂肪酸を飽和脂肪酸の形態、すなわちパルミチン酸(16:0)およびステアリン酸(18:0)の両方の形態で15%〜45%有するヒマワリ系統は幾つか存在する。2種類の系統を用いた:1)高ステアリン系統、すなわちステアリン酸含量が当該種子の油中、全脂肪酸の15%〜45%のもの、および2)高パルミチン系統、すなわちパルミチン酸含量が当該種子の油中、全脂肪酸の15%〜45%であって、パルミトレイン酸(16:1)含量が当該種子の油中、全脂肪酸の5%〜15%のもの。
The oil was obtained by recombining the following individual features that have been previously developed in sunflower:
a) High saturated fatty acid content. There are several sunflower lines in the seed oil that have 15% to 45% fatty acids in the form of saturated fatty acids, both palmitic acid (16: 0) and stearic acid (18: 0). Two types of lines were used: 1) high stearin line, ie stearic acid content of 15% to 45% of total fatty acids in the oil of the seed, and 2) high palmitic line, ie palmitic acid content, of the seed 15% to 45% of the total fatty acids, and palmitoleic acid (16: 1) content is 5% to 15% of the total fatty acids in the oil of the seed.
b)オレイン酸(18:1)含量が高いこと。使用される「高オレイン」と呼ばれるヒマワリ系統は当該種子の油中、脂肪酸をオレイン酸の形態で85%〜95%有するものである。リノール酸(18:2)含量は当該種子の油中、全脂肪酸の2%〜10%である。 b) High oleic acid (18: 1) content. The sunflower line called “high olein” used has a fatty acid in the form of oleic acid in the seed oil of 85% to 95%. The linoleic acid (18: 2) content is 2% to 10% of the total fatty acids in the seed oil.
c)ガンマ−トコフェロールおよびデルタ−トコフェロールの合計含量が高いこと。この特徴は幾つかのヒマワリ系統において存在し、当該系統において両方のトコフェロールの合計量は当該種子中に存在する全トコフェロールの85%よりも多い。2種類の系統を用いた:1)高ガンマ−トコフェロール系統、すなわちガンマ−トコフェロール含量が種子中の全トコフェロールの85%よりも多く、最高で、種子中の全トコフェロールの99%までの値に達し得るもの、および2)高デルタ−トコフェロール系統、すなわちデルタ−トコフェロール含量が種子中の全トコフェロールの65%よりも多く、かつガンマ−トコフェロール含量が種子中の全トコフェロールの20%よりも多く、デルタ−トコフェロールとガンマ−トコフェロールとの合計量が種子中の全トコフェロールの85%よりも多く、最高で、種子中の全トコフェロールの99%までの値に達し得るもの。両方の系統の種子は、全トコフェロール含量が油1kgあたり500〜1500mgであって、前記したトコフェロール分布を有する油をもたらす。 c) High total content of gamma-tocopherol and delta-tocopherol. This feature is present in several sunflower lines, where the total amount of both tocopherols is greater than 85% of the total tocopherols present in the seed. Two lines were used: 1) High gamma-tocopherol lines, ie gamma-tocopherol content was greater than 85% of total tocopherols in seeds, reaching values up to 99% of total tocopherols in seeds And 2) a high delta-tocopherol line, i.e. a delta-tocopherol content greater than 65% of the total tocopherol in the seed and a gamma-tocopherol content greater than 20% of the total tocopherol in the seed, The total amount of tocopherol and gamma-tocopherol is greater than 85% of the total tocopherol in the seed and can reach a value up to 99% of the total tocopherol in the seed. The seeds of both lines have an overall tocopherol content of 500-1500 mg / kg of oil, resulting in an oil having the tocopherol distribution described above.
これらの特徴は遺伝的複雑度(genetic complexity)が高いので、組換えは以下に説明する2つの工程で行った:
1)「飽和脂肪酸の含量が高い」特徴と「オレイン酸の含量が高い」特徴の組換え
飽和脂肪酸(パルミチン酸およびステアリン酸)含量が高い系統と、オレイン酸含量が高い系統との間で、制御交雑(controlled crossbreedings)を行い、F1雑種種子を得た。この種子を生長させ、対応する植物を自花受精させてF2種子を得たところ、当該種子は両方の特徴に対して分離(segregation)を示した。個々の特徴のそれぞれは、ほとんどが劣性の1−3遺伝子によって制御されるため、求める特徴、すなわち高い飽和脂肪酸含量と高いオレイン酸含量という特徴を併有する種子を得るためには、各々の交雑あたり平均100個のF2種子を分析する必要があった。当該2つの特徴が組み合わされた種子の発生頻度は低いため、当該2つの特徴が組み合わされた種子を十分な数で得るためには、各々の交雑あたり平均2000個の種子を分析する必要があった。
Because these features have high genetic complexity, recombination was performed in two steps as described below:
1) Recombinant with the feature of "high saturated fatty acid content" and "high oleic acid" characteristics between the line with high saturated fatty acid (palmitic acid and stearic acid) content and the line with high oleic acid content, It performs control hybridization (controlled crossbreedings), to give the F 1 hybrid seed. The seeds were grown and where the corresponding plant to obtain a Jihana fertilized allowed to F 2 seeds, the seeds showed separation for both characteristics (segregation). Each individual characteristic is mostly controlled by the recessive 1-3 gene, so to obtain seeds that have the desired characteristics, i.e. the characteristics of high saturated fatty acid content and high oleic acid content, for each cross it was necessary to analyze a mean of 100 F 2 seeds. Since the occurrence frequency of seeds combining the two characteristics is low, it is necessary to analyze an average of 2000 seeds for each cross in order to obtain a sufficient number of seeds combining the two characteristics. It was.
改良された脂肪酸分布の特徴の組み合わせが商業的に有用であるためには、当該特徴は、遺伝性がなければならないし、ヒマワリ植物が栽培される環境条件とは無関係に発現されなければならない。このため、選択法(selection process)を実施して、当該特徴を定着(fixing)させ、かつ様々な環境条件下での該特徴の安定性を確かめた。この目的のために、選択されたF2種子をまき、各々のF2植物の自花受精から生じるF3種子、ならびに幾つかの環境で栽培された多くのF3植物から生じるF4種子の分析により、組み合わされた特徴の遺伝的安定性を確認した。 In order for a combination of improved fatty acid distribution characteristics to be commercially useful, the characteristics must be heritable and expressed independently of the environmental conditions in which the sunflower plant is grown. For this reason, a selection process was performed to fix the feature and to confirm the stability of the feature under various environmental conditions. For this purpose, selected F 2 seeds are seeded and F 3 seeds arising from the self-fertilization of each F 2 plant, as well as F 4 seeds arising from many F 3 plants grown in several environments. Analysis confirmed the genetic stability of the combined features.
この第1工程の結果として、油中に存在する全脂肪酸の15%〜45%という高含量の飽和脂肪酸、全脂肪酸の45%〜75%という高含量のオレイン酸、および全脂肪酸の10%未満という低含量のリノール酸を含有する種子をもたらす植物を得た。 As a result of this first step, a high content of saturated fatty acids of 15% to 45% of the total fatty acids present in the oil, a high content of oleic acid of 45% to 75% of the total fatty acids, and less than 10% of the total fatty acids A plant yielding seeds containing a low content of linoleic acid was obtained.
2)新規な「飽和脂肪酸の含量が高く、かつオレイン酸の含量が高い」特徴と「ガンマ−およびデルタ−トコフェロールの合計含量が高い」特徴の組換え
この第2工程では、先の工程1)で得られた高い飽和脂肪酸含量(油中に存在する全脂肪酸の15〜45%)および高いオレイン酸含量(油中に存在する全脂肪酸の45〜75%)を組み換えた植物、ならびにガンマ−トコフェロールとデルタ−トコフェロールの合計含量が高い(種子中に存在する全トコフェロールの85%よりも多い)植物を用いた。
2) Recombination of novel “high saturated fatty acid content and high oleic acid” characteristics and “high total content of gamma- and delta-tocopherol” characteristics In this second step, the previous step 1) Recombined plants with high saturated fatty acid content (15-45% of total fatty acids present in oil) and high oleic acid content (45-75% of total fatty acids present in oil) obtained from the above, and gamma-tocopherol And plants with a high total content of delta-tocopherol (greater than 85% of the total tocopherol present in the seed) were used.
ガンマ−およびデルタ−トコフェロールの合計含量が高い系統と、飽和脂肪酸含量が高くかつオレイン酸含量が高いF3植物との間で、制御交雑を行った後、F1雑種種子を得た。この種子を生長させ、対応する植物を自花受精させてF2種子を得たところ、当該種子は組換えの目的とする3つの特徴、すなわち高い飽和脂肪酸(パルミチン酸およびステアリン酸)含量、高いオレイン酸含量および高いガンマ−およびデルタ−トコフェロール合計含量に対して分離を示した。求める脂肪酸分布は4−6遺伝子によって制御され、また求めるトコフェロール分布は一般的に劣性の1−3遺伝子によって制御されるため、求める特徴、すなわち高い飽和脂肪酸含量、高いオレイン酸含量、および高いガンマ−およびデルタ−トコフェロール合計含量を併有する種子を得るためには、各々の交雑あたり平均400個のF2種子を分析する必要があった。当該2つの特徴が組み合わされた種子の発生頻度は低いため、当該2つの特徴が組み合わされた種子を十分な数で得るためには、各々の交雑あたり平均5000個の種子を分析する必要があった。 Gamma - and delta - the total content higher strains of tocopherol, between high and oleic acid content of saturated fatty acid content is higher F 3 plants, after the control crossbred to obtain F 1 hybrid seed. The seeds were grown and was in the corresponding plants were Jihana fertilized to obtain an F 2 seeds, the seeds are three features of interest of recombinant, or high saturated fatty acids (palmitic acid and stearic acid) content, high Separation was shown for oleic acid content and high gamma- and delta-tocopherol total content. Since the desired fatty acid distribution is controlled by the 4-6 gene and the desired tocopherol distribution is generally controlled by the recessive 1-3 gene, the desired characteristics are high: high saturated fatty acid content, high oleic acid content, and high gamma − and delta - in order to obtain seeds having both tocopherol sum content, it was necessary to analyze the average per each hybrid 400 of the F 2 seed. Since the frequency of seeds combining the two features is low, it is necessary to analyze an average of 5000 seeds for each cross in order to obtain a sufficient number of seeds combining the two features. It was.
改良された脂肪酸分布の特徴の組み合わせが商業的に有用であるためには、当該特徴は、遺伝性がなければならないし、ヒマワリ植物が栽培される環境条件とは無関係に発現されなければならない。このため、選択法を実施して、当該特徴を定着させ、かつ様々な環境条件下での該特徴の安定性を確かめた。この目的のために、選択されたF2種子をまき、各々のF2植物のF3種子、ならびに多くのF3植物から生じるF4種子の分析により、組み合わされた特徴の遺伝的安定性を確認した。これらの植物は、様々な環境で培養された。この結果、高い飽和脂肪酸含量、高いオレイン酸含量および高いガンマ−およびデルタ−トコフェロール合計含量の同時発現が、植物の培養条件とは無関係に発現される定着された安定な遺伝的性質の結果であることが確認された。 In order for a combination of improved fatty acid distribution characteristics to be commercially useful, the characteristics must be heritable and expressed independently of the environmental conditions in which the sunflower plant is grown. For this reason, a selection method was implemented to establish the feature and to confirm the stability of the feature under various environmental conditions. For this purpose, sown F 2 seeds are selected, F 3 seeds of each of the F 2 plants, as well as the analysis of F 4 seeds originating from a number of F 3 plants, the genetic stability of the combined features confirmed. These plants were cultured in a variety of environments. As a result, the co-expression of high saturated fatty acid content, high oleic acid content and high total gamma- and delta-tocopherol content is the result of established and stable genetic properties that are expressed independently of plant culture conditions It was confirmed.
この第2工程の結果として、油中に存在する全脂肪酸の15%〜45%という高含量の飽和脂肪酸、全脂肪酸の45%〜75%という高含量のオレイン酸、油中に存在する全トコフェロールの85%よりも多いという高い合計含量のガンマ−トコフェロールおよびデルタ−トコフェロールを含有する種子をもたらす植物を得た。飽和脂肪酸の源がパルミチン酸含量の高い系統(油中の全脂肪酸の15〜45%)であったときは、油中の全脂肪酸の5%よりも多い量でのパルミトレイン酸の存在も観察された。 As a result of this second step, a high content of saturated fatty acid of 15% to 45% of the total fatty acid present in the oil, a high content of oleic acid of 45% to 75% of the total fatty acid, total tocopherol present in the oil Plants were obtained that resulted in seeds containing a high total content of gamma-tocopherol and delta-tocopherol, greater than 85% of When the source of saturated fatty acids is a strain with a high palmitic acid content (15-45% of the total fatty acids in the oil), the presence of palmitoleic acid in an amount greater than 5% of the total fatty acids in the oil is also observed. It was.
異なる組換え工程において用いられるヒマワリ系統の脂肪酸(パルミチン酸、ステアリン酸およびオレイン酸)およびトコフェロールの含量範囲を考慮すると、本発明において行われる特定の実施態様には、ステアリン酸含量が油中に存在する全脂肪酸の15%よりも多く、また25%よりも多く、さらには35%よりも多い油が包含される。本発明の他の実施態様には、パルミチン酸含量が油中に存在する全脂肪酸の15%よりも多く、また25%よりも多く、さらには35%よりも多い油が包含される。 In view of the content range of sunflower fatty acids (palmitic acid, stearic acid and oleic acid) and tocopherol used in different recombination processes, a specific embodiment carried out in the present invention has a stearic acid content present in the oil. More than 15%, more than 25% and even more than 35% of the total fatty acids are included. Other embodiments of the invention include oils having a palmitic acid content of greater than 15%, greater than 25%, and even greater than 35% of the total fatty acids present in the oil.
本発明の2つの他の実施態様においては、本発明の油のガンマ−トコフェロール含量は、油中に存在する全トコフェロールの85%よりも多く、さらには95%よりも多い。 In two other embodiments of the present invention, the gamma-tocopherol content of the oils of the present invention is greater than 85% and even greater than 95% of the total tocopherols present in the oil.
本発明の他の実施態様においては、当該油のデルタ−トコフェロール含量は、油中に存在する全トコフェロールの25%よりも多く、また55%よりも多く、さらには75%よりも多い。 In other embodiments of the invention, the delta-tocopherol content of the oil is greater than 25%, greater than 55%, and even greater than 75% of the total tocopherol present in the oil.
上記した植物によって産生された種子から抽出される油は、植物油の酸化および低い熱安定性の主要な原因となる不飽和度が低い脂肪酸分布により、また酸化および高温の影響に対する保護作用が強いトコフェロールの高比率での存在により、従来のどのヒマワリ油よりも非常に優れた熱安定性を示し、また改良された脂肪酸分布またはトコフェロール分布しか有さない他のどのヒマワリ油よりも非常に優れた熱安定性を示す。 The oil extracted from the seeds produced by the plants mentioned above is a tocopherol with a strong protection against the effects of oxidation and high temperature due to the low unsaturation fatty acid distribution which is the main cause of vegetable oil oxidation and low thermal stability Presents a much better heat stability than any other sunflower oil, and much better heat than any other sunflower oil that has only an improved fatty acid distribution or tocopherol distribution. Shows stability.
本発明の対象とする油の油安定性指数(OSI)は、未精製油における温度110℃での10時間の誘導期の後、ランシマット型743装置(メトローム社製、ヘリザウ、スイス国)で測定され、35〜120時間である。 The oil stability index (OSI) of the oil subject to the present invention is measured with a Rancimat type 743 device (Metrohm, Herisau, Switzerland) after an induction period of 10 hours at a temperature of 110 ° C. in the unrefined oil. 35 to 120 hours.
加熱時において油中に存在するトコフェロールの分解ならびに極性化合物およびポリマーの生成を検討することにより、油の熱的酸化分解(thermo-oxidative degradation)について評価する。本発明の対象とする油は、親種子として使用される種子から得られた油よりも、熱的酸化分解が少ないし、ポリマーおよび極性化合物の形成の割合が低い(半分)。 The thermal-oxidative degradation of the oil is evaluated by examining the degradation of tocopherols present in the oil during heating and the formation of polar compounds and polymers. The oils targeted by the present invention have less thermal oxidative degradation and a lower rate of formation of polymers and polar compounds (half) than oils obtained from seeds used as parent seeds.
油安定性が高く、熱的酸化分解に対する耐性が高い本発明の油は、これらの技術的特性が付与されているので、ヒトおよび/または動物の食物に安定的に使用できる。本発明の油はまた、バイオ潤滑油および/またはバイオ燃料の製造にも使用できる。 The oil of the present invention, which has high oil stability and high resistance to thermal oxidative degradation, can be stably used in human and / or animal foods because of these technical characteristics. The oils of the present invention can also be used in the production of biolubricating oils and / or biofuels.
本発明の1つの実施態様において、本発明の油は、スコットランドのアバディーン(Aberdeen)所在のエヌ・シー・アイ・エム・ビー(NCIMB)(ナショナル・コレクション・オブ・インダストリアル・マリン・アンド・フード・バクテリア(National Collection of Industrial, Marine and Food Bacteria))社に2007年3月20日付で寄託番号NCIMB−41477にて寄託された種子系統(seed line)IAS−1265のヒマワリの種子に由来する抽出物から得ることができる。 In one embodiment of the present invention, the oil of the present invention comprises NCIMB (National Collection of Industrial Marine and Foods, Aberdeen, Scotland). Extract derived from sunflower seeds of seed line IAS-1265 deposited at NCIMB-41477 on March 20, 2007 with Bacteria (National Collection of Industrial, Marine and Food Bacteria) Can be obtained from
本発明の油を含有する複数の油の混合物に加えて、当該ヒマワリ種子から油を抽出するための抽出工程の残渣として得られる粉体もまた本発明の対象である。 In addition to a mixture of a plurality of oils containing the oil of the present invention, powders obtained as a residue of an extraction process for extracting oil from the sunflower seeds are also an object of the present invention.
本発明の別の対象は、本発明の油の特性を有する油を含有するヒマワリの種子である。それらの種子は結果として特定の植物が得られる種子であり、当該植物は、自花受精により、生長後に自身の種子中に、当該植物の栽培条件とは無関係に、本発明の油の特性を有する油を含有する植物である。1つの実施態様においては、本発明の種子は、スコットランドのアバディーン所在のエヌ・シー・アイ・エム・ビー社の種子銀行に2007年3月20日付で寄託番号NCIMB−41477にて寄託されたヒマワリ系統IAS−1265から得られる。本発明の対象する種子は、本発明の油を得るために用いることができる。 Another subject of the present invention is sunflower seeds containing oils having the characteristics of the oils of the present invention. These seeds are seeds that result in the production of a specific plant, and the plant has the characteristics of the oil of the present invention in its own seeds after growth by self-fertilization, regardless of the cultivation conditions of the plant. It is a plant containing the oil it has In one embodiment, the seeds of the present invention are sunflowers deposited at the seed bank of NCB, Aberdeen, Scotland, on deposit number NCIMB-41477, dated 20 March 2007. Obtained from line IAS-1265. The target seed of the present invention can be used to obtain the oil of the present invention.
自花受精により、本発明の油を含有する種子を産生するヒマワリ植物(ヘリアンサス・アニュース・エル)もまた、本発明の別の対象である。 Sunflower plants (Helianthus anews L) that produce seeds containing the oil of the invention by self-fertilization are also another subject of the invention.
種子の入手
5.1 「飽和脂肪酸含量が高い」特徴および「オレイン酸含量が高い」特徴の組換え
油中のパルミチン酸含量が高く(全脂肪酸の15%よりも多い)、かつ化学的な突然変異誘発によって発育させたヒマワリ系統NP−40、および油中のオレイン酸含量が高い(全脂肪酸の85%よりも多い)ヒマワリ系統BSD−2−423のそれぞれについて、48個の種子を無作為に取り出し、個々の種子のそれぞれについて油中の酸の組成または分布を分析した。分析後に種子は生長できなければならないために、種子の分析は破壊的であってはならないので、当該分析はハーフ種子法(half seed process)によって行った。当該方法は、裁断が種子の生長能に影響を及ぼさないように、胚に対して種子末端の少量部分を裁断することからなる。その後、裁断部分はその脂肪酸分布について、脂肪酸のメチルエステルのガスクロマトグラフィーにより分析し(アール・ガーシェス(R. Garces)およびエム・マンチャ(M. Mancha)、「新鮮な植物組織からの一段階での脂質の抽出と脂肪酸メチルエステルの調製」、分析生化学(Analytical Biochemistry)、第211巻:第139−143頁、1993年)、胚を含む当該種子の残りは、生長が当該分析結果に依存して起こる最適条件にて貯蔵する。
5.1 Seed acquisition 5.1 Recombinant oil with high saturated fatty acid and high oleic acid characteristics High palmitic acid content (more than 15% of total fatty acids) and chemical suddenness 48 seeds were randomly selected for each of the sunflower lines NP-40 grown by mutagenesis and the sunflower lines BSD-2-423 with high oleic acid content in oil (more than 85% of total fatty acids) Removed and analyzed the composition or distribution of the acid in the oil for each individual seed. Since the seed analysis must not be destructive since the seed must be able to grow after the analysis, the analysis was performed by the half seed process. The method consists of cutting a small portion of the seed end against the embryo so that the cutting does not affect seed growth. The cut portion was then analyzed for its fatty acid distribution by gas chromatography of fatty acid methyl esters (R. Garces and M. Mancha), “in one step from fresh plant tissue. Extraction of Lipids and Preparation of Fatty Acid Methyl Esters ”, Analytical Biochemistry, 211: 139-143, 1993), the rest of the seed including embryos depends on the results of the analysis Store at the optimal conditions that occur.
各種子の脂肪酸分布を確認した後、当該種子を生長させ、対応する植物を温室で栽培し、NP−40植物とBSD−2−423植物との間で制御交雑を行った。当該交雑は、雌親として用いられる予定の植物において葯が開いて花粉を放つ前、明け方に花の雄蕊またはおしべを除去し、その後、雄親として用いられる予定の植物の花粉を用いて人工授粉することからなる。本実施例では、雌親としてBSD−2−423植物を用い、雄親としてNP−40植物を用いたが、親を反対に用いても同じ結果が得られる。 After confirming the fatty acid distribution of each seed, the seed was grown, the corresponding plant was cultivated in a greenhouse, and a controlled cross was performed between the NP-40 plant and the BSD-2-423 plant. The crossing involves artificial pollination using the pollen of the plant that is to be used as a male parent, after removing the stamens or stamens of the flower at dawn before the buds open and pollen is released in the plant that is to be used as the female parent. Made up of. In this example, the BSD-2-423 plant was used as the female parent and the NP-40 plant was used as the male parent.
当該交雑から得られた雑種種子は、F1種子と呼ぶものとし、上記で説明したハーフ種子法により脂肪酸分布について分析した。F1種子におけるパルミチン酸の平均含量は油中の全脂肪酸の7.3%であり、一方、NP−40植物の種子における対応する値は30.0%であり、また、BSD−2−423植物の種子における対応する値は3.5%であった。F1種子におけるオレイン酸の平均含量は油中の全脂肪酸の69.8%であり、一方、NP−40種子における対応する値は8.0%であり、また、BSD−2−423種子における対応する値は89.6%であった。 Hybrid seeds obtained from the crosses, and be referred to as F 1 seeds, were analyzed for their fatty acid profile by the half seed process described above. The average palmitic acid content in F 1 seeds was 7.3% of the total fatty acids in the oil, the value corresponding in seeds of NP-40 plants are 30.0%, also, BSD-2-423 The corresponding value in plant seeds was 3.5%. The average content of oleic acid in the F 1 seed is 69.8% of the total fatty acids in the oil, while the corresponding value in the NP-40 seed is 8.0%, and in the BSD-2-423 seed The corresponding value was 89.6%.
150個のF1種子を生長させ、対応する植物を自花受精させて、F2種子を得、脂肪酸分布について分析した。2348個のF2種子を分析し、パルミチン酸含有量とオレイン酸含有量を調べた。F2種子におけるパルミチン酸含量は油中の全脂肪酸の3.1%〜37.8%であった。F2種子におけるオレイン酸含量は油中の全脂肪酸の6.9%〜92.2%の範囲で変化した。分析した2348個の種子のうち、104個の種子は、油中の全脂肪酸に対して15%よりも多い高パルミチン酸含量と、45%よりも多い高オレイン酸含量を示した。これらの104個の種子のうち、パルミチン酸含量がより高い種子は全脂肪酸に対して34%のパルミチン酸含量および55%のオレイン酸含量を示したが、オレイン酸含量がより高い種子は全脂肪酸に対して18%のパルミチン酸含量および73%のオレイン酸含量を示した。 Grown to 150 of F 1 seeds, and the corresponding plants were Jihana fertilized to obtain an F 2 seeds were analyzed for their fatty acid profile. Analyzing the 2348 pieces of F 2 seeds were examined palmitic acid content and oleic acid content. Palmitic acid content in the F 2 seeds was 3.1% ~37.8% of the total fatty acids in the oil. Oleic acid content in the F 2 seeds showed a variation 6.9% ~92.2% of the total fatty acids in the oil. Of the 2348 seeds analyzed, 104 seeds showed a high palmitic acid content of more than 15% and a high oleic acid content of more than 45% relative to the total fatty acids in the oil. Of these 104 seeds, seeds with higher palmitic acid content showed 34% palmitic acid content and 55% oleic acid content relative to total fatty acids, while seeds with higher oleic acid content showed total fatty acids. Showed a palmitic acid content of 18% and an oleic acid content of 73%.
選択されたF2種子をまき、組み合わされた特徴の遺伝的安定性を、各々のF2植物のF3種子の分析により確認した。全3744個のF3種子の分析の結果、平均含量で27.7%±3.4%(平均値±標準偏差)のパルミチン酸、7.2%±1.7%のパルミトレイン酸、1.4%±0.3%のステアリン酸、59.8%±4.9%のオレイン酸、および3.9%±1.0%のリノール酸からなる種子油の脂肪酸組成を得た。 Selected F 2 seeds were sown and the genetic stability of the combined characteristics was confirmed by analysis of the F 3 seeds of each F 2 plant. Analysis of a total of 3744 F 3 seeds revealed that the average content was 27.7% ± 3.4% (mean value ± standard deviation) palmitic acid, 7.2% ± 1.7% palmitoleic acid, The fatty acid composition of a seed oil consisting of 4% ± 0.3% stearic acid, 59.8% ± 4.9% oleic acid, and 3.9% ± 1.0% linoleic acid was obtained.
5.2 「飽和脂肪酸含量が高く、かつオレイン酸含量が高い」特徴と「ガンマ−およびデルタ−トコフェロールの合計含量が高い」特徴の組換え
先の工程で得られたF3種子であって、高パルミチン酸含量(15%よりも多い)と高オレイン酸含量(45%よりも多い)とが組み合わされた種子を48個取り出し、当該種子と、ガンマ−トコフェロール含量が高い(85%よりも多い)T2100系統の48個の種子とのそれぞれについて、油中の酸組成または分布およびトコフェロール組成または分布の両方を分析した。この分析は上記したハーフ種子法により行った。種子の裁断部分を2つに分け、一方の1/2では脂肪酸のメチルエステルのガスクロマトグラフィー(アール・ガーシェス(R. Garces)およびエム・マンチャ(M. Mancha)、1993年、上記の文献)により脂肪酸分布を分析し、他方の1/2では高性能液体クロマトグラフィー−HPLC(エフ・ゴッフマン(F. Goffman)等、「なたね(バルシカ・ナプス・エル(Brassica napus L.))の単一種子におけるトコフェロールの定量的測定」、フェット(Fett)/リピッド(Lipid)、第101巻、第142−145頁、1999年)によりトコフェロール分布を分析した。
5.2 "saturated fatty acid content is high and oleic acid content higher" features and a "gamma - high tocopherol sum content - and delta" F 3 seeds obtained in the recombinant preceding step features, 48 seeds with a combination of high palmitic acid content (greater than 15%) and high oleic acid content (greater than 45%) are removed and the seed and gamma-tocopherol content is high (greater than 85%) ) For each of the 48 seeds of the T2100 line, both the acid composition or distribution in oil and the tocopherol composition or distribution were analyzed. This analysis was performed by the half seed method described above. Seed cuttings are divided into two parts, one half of which is gas chromatography of fatty acid methyl esters (R. Garces and M. Mancha, 1993, supra) Fatty acid distribution was analyzed by HPLC, and in the other half, high-performance liquid chromatography-HPLC (F. Goffman et al., “Natane (Brassica napus L.) single Tocopherol distribution was analyzed by "Quantitative measurement of tocopherol in seeds", Fett / Lipid, 101, 142-145, 1999).
各種子の脂肪酸およびトコフェロール分布を確認した後、当該種子を生長させ、対応する植物を温室で栽培し、F3種子から生じる植物とT2100植物との間の制御交雑を、5.1欄に記載の方法と同様にして行った。F1種子中の脂肪酸およびトコフェロール分布について分析した。F1種子におけるパルミチン酸の平均含量は油中の全脂肪酸の6.8%であり、一方、NP−40植物の種子における対応する値は28.9%であり、また、T2100植物の種子における対応する値は3.2%であった。F1種子におけるオレイン酸含量は油中の全脂肪酸の72.6.8%であり、一方、BSD−2−423種子における対応する値は90.3%であり、または、T2100種子における対応する値は12.1%であった。F1種子におけるガンマ−トコフェロール含量は全トコフェロールの1.2%であり、対照として使用したNP−40種子およびBSD−2−423種子における対応する値は0.0%であり、また、T2100種子における対応する値は99.2%であった。 After confirming the fatty acid and tocopherol profile of each seed, grown the seeds were cultivated corresponding plants in a greenhouse, the control cross between the plant and the T2100 plants resulting from F 3 seeds, according to 5.1 column It was performed in the same manner as the above method. It was analyzed for fatty acid and tocopherol profile of F 1 seeds. The average content of palmitic acid in the F 1 seed is 6.8% of the total fatty acids in the oil, while the corresponding value in the seed of the NP-40 plant is 28.9%, and in the seed of the T2100 plant The corresponding value was 3.2%. The oleic acid content in the F 1 seed is 72.6.8% of the total fatty acids in the oil, while the corresponding value in the BSD-2-423 seed is 90.3%, or the corresponding value in the T2100 seed The value was 12.1%. The gamma-tocopherol content in the F 1 seed is 1.2% of the total tocopherol, the corresponding value in the NP-40 seed and BSD-2-423 seed used as controls is 0.0%, and T2100 seed The corresponding value for was 99.2%.
100個のF1種子を生長させ、対応する植物を自花受精させて、F2種子を得、脂肪酸分布について分析した。8952個のF2種子を分析し、パルミチン酸含有量とオレイン酸含有量とガンマ−トコフェロール含有量を調べた。F2種子におけるパルミチン酸含量は油中の全脂肪酸の2.2%〜37.6%であった。F2種子におけるオレイン酸含量は油中の全脂肪酸の5.8%〜94.2%の範囲で変化した。ガンマ−トコフェロール含量は種子中の全トコフェロールの0.0%〜99.6%の範囲で変化した。分析した8952個の種子のうち、51個の種子は、全脂肪酸の15%よりも多い高パルミチン酸含量と、油中の全脂肪酸の45%よりも多い高オレイン酸含量と、種子中の全トコフェロールの85%よりも多い高ガンマ−トコフェロール含量とを示した。 Grown to 100 F 1 seeds, and the corresponding plants were Jihana fertilized to obtain an F 2 seeds were analyzed for their fatty acid profile. Analyzing the 8952 pieces of F 2 seeds, palmitic acid content and oleic acid content and the gamma - examined the tocopherol content. Palmitic acid content in the F 2 seeds was 2.2% ~37.6% of the total fatty acids in the oil. Oleic acid content in the F 2 seeds showed a variation 5.8% ~94.2% of the total fatty acids in the oil. The gamma-tocopherol content varied from 0.0% to 99.6% of the total tocopherol in the seed. Of the 8952 seeds analyzed, 51 seeds had a high palmitic acid content of more than 15% of the total fatty acids, a high oleic acid content of more than 45% of the total fatty acids in the oil, and total seeds in the seeds. It showed a high gamma-tocopherol content greater than 85% of tocopherol.
選択されたF2種子をまき、組み合わされた特徴の遺伝的安定性を、各々のF2植物のF3種子の分析により確認した。全3204個のF3種子の分析の結果、平均含量で28.9%±3.3%(平均値±標準偏差)のパルミチン酸、7.3%±1.1%のパルミトレイン酸、1.6%±0.5%のステアリン酸、52.5%±3.9%のオレイン酸、および4.2%±0.7%のリノール酸からなる種子油の脂肪酸組成、ならびに2.8%±1.3%のアルファ−トコフェロール、96.6%±1.8%のガンマ−トコフェロールおよび0.6%±0.2%のデルタ−トコフェロールからなるトコフェロール画分(fraction)の組成を得た。 Selected F 2 seeds were sown and the genetic stability of the combined characteristics was confirmed by analysis of the F 3 seeds of each F 2 plant. Analysis of a total of 3204 F 3 seeds revealed that the average content was 28.9% ± 3.3% (mean value ± standard deviation) palmitic acid, 7.3% ± 1.1% palmitoleic acid, Fatty acid composition of seed oil consisting of 6% ± 0.5% stearic acid, 52.5% ± 3.9% oleic acid, and 4.2% ± 0.7% linoleic acid, and 2.8% A composition of tocopherol fractions consisting of ± 1.3% alpha-tocopherol, 96.6% ± 1.8% gamma-tocopherol and 0.6% ± 0.2% delta-tocopherol was obtained. .
油の抽出
150gのF3種子を用い、石油エーテル(沸点40〜60℃)およびソックスレー抽出系により、スペイン標準化協会による方法(標準カタログ、マドリッド、1991年)に従って油を抽出した。油中の脂肪酸およびトコフェロール組成について分析し、その結果、29.2%のパルミチン酸、7.5%のパルミトレイン酸、1.7%のステアリン酸、52.4%のオレイン酸、および4.2%のリノール酸からなる脂肪酸組成、ならびに2.4%のアルファ−トコフェロール、96.4%のガンマ−トコフェロールおよび1.2%のデルタ−トコフェロールからなるトコフェロール画分の組成を得た。
With F 3 seeds of oil extraction 150 g, petroleum ether (b.p. 40 to 60 ° C.) and a Soxhlet extraction system, the method according to the Spanish Standardization Association (standard catalog, Madrid, 1991) was extracted oil in accordance. Analysis of fatty acid and tocopherol composition in the oil results in 29.2% palmitic acid, 7.5% palmitoleic acid, 1.7% stearic acid, 52.4% oleic acid, and 4.2 A fatty acid composition consisting of% linoleic acid and a tocopherol fraction consisting of 2.4% alpha-tocopherol, 96.4% gamma-tocopherol and 1.2% delta-tocopherol were obtained.
得られた油の技術的特性
a)様々な種類のヒマワリ油における油安定性指数(OSI)の測定
米国オイル化学者協会(米国オイル化学者協会の公式方法および推奨する方法、第4版、AOCS、シャンペーン、イリノイ州、米国、1994年)の標準プロトコルに従って、以下の種類のヒマワリ油について、110℃で10時間加熱した後、油安定性指数(OSI)を測定した。
油1:標準ヒマワリ油(標準的な脂肪酸およびトコフェロール分布)
油2:オレイン酸含量が高く、かつトコフェロール分布が標準的な油
油3:パルミチン酸含量が高く、オレイン酸含量が高く、かつトコフェロール分布が標準的な油
油4:パルミチン酸含量が高く、オレイン酸含量が高く、かつトコフェロール分布が改良された(ガンマ−トコフェロール含量が高い)本発明の油。
Technical characteristics of the resulting oils a) Determination of oil stability index (OSI) in various types of sunflower oil American Oil Chemists Association (official and recommended methods of the American Oil Chemists Association, 4th edition, AOCS According to the standard protocol of Champaign, Illinois, USA, 1994), the following types of sunflower oil were heated at 110 ° C. for 10 hours and then the oil stability index (OSI) was measured.
Oil 1: standard sunflower oil (standard fatty acid and tocopherol distribution)
Oil 2: Oil with high oleic acid content and standard tocopherol distribution Oil 3: Oil with high palmitic acid content, high oleic acid content and standard tocopherol distribution Oil 4: High palmitic acid content, olein The oil of the present invention having a high acid content and improved tocopherol distribution (high gamma-tocopherol content).
4種類のヒマワリ油の脂肪酸およびトコフェロール組成ならびに110℃で10時間加熱後のOSIを表2に示す: The fatty acid and tocopherol compositions of the four sunflower oils and the OSI after heating at 110 ° C. for 10 hours are shown in Table 2:
a16:0=パルミチン酸; 18:0=ステアリン酸; 18:1=オレイン酸; 18:2=リノール酸; 16:1 パルミトレイン酸
bA−T=アルファ−トコフェロール; B−T=ベータ−トコフェロール; G−T=ガンマ−トコフェロール; D−T=デルタ−トコフェロール
a 16: 0 = palmitic acid; 18: 0 = stearic acid; 18: 1 = oleic acid; 18: 2 = linoleic acid; 16: 1 palmitoleic acid
b AT = alpha-tocopherol; BT = beta-tocopherol; GT = gamma-tocopherol; DT = delta-tocopherol
b)加熱時におけるトコフェロールの分解ならびに極性化合物およびポリマーの生成に関する検討
油中において既に改良された脂肪酸分布におけるトコフェロール分布改良の相乗効果を検討するために、a)欄で記載の油3および油4を長時間(25時間)の高温(180℃)に付し、油の熱的酸化分解に直接的に関係する以下のパラメータを測定した:
b) Study on decomposition of tocopherol during heating and formation of polar compounds and polymers In order to examine the synergistic effect of improved tocopherol distribution in the already improved fatty acid distribution in oil, oil 3 and oil 4 described in column a) Was subjected to a high temperature (180 ° C.) for a long time (25 hours) and the following parameters directly related to the thermal oxidative degradation of the oil were measured:
−全トコフェロール含量;当該トコフェロール含量は油1kgあたりのトコフェロールの総mg数で表し、国際純正応用化学連合(IUPAC、「油、脂肪および誘導体の分析のための標準的方法」、第7版の第1増補、パーガモン(Pergamon)出版、オックスフォード、英国、1992年)の標準的方法に従って測定した。
−極性化合物の形成は油の総重量に対する割合(%)で表し、エム・シー・ドバーガンス(M.C. Dobarganes)等によって記述された方法に従って測定した(「加熱された脂肪および非加熱の脂肪における極性化合物の高性能サイズ排除クロマトグラフィー」、ファット・サイエンス・アンド・テクノロジー(Fat Science and Technology)、第90巻、第308−311頁、1988年)。
−ポリマーの形成は油の総重量に対する割合%で表し、国際純正応用化学連合(IUPAC、上記の研究)の標準的方法に従って測定した。
結果を表3に示す。
-Total tocopherol content; the tocopherol content is expressed as the total mg of tocopherol per kg of oil and is defined by the International Union of Applied Chemistry (IUPAC, "Standard Method for Analysis of Oils, Fats and Derivatives", 7th edition 1 augmentation, published by Pergamon, Oxford, UK, 1992).
-Polar compound formation is expressed as a percentage of the total weight of the oil and measured according to the method described by MC Dobarganes et al. ("Polar compounds in heated and unheated fats" High Performance Size Exclusion Chromatography ", Fat Science and Technology, 90, 308-311, 1988).
-Polymer formation is expressed as a percentage of the total weight of oil and was measured according to standard methods of the International Pure Applied Chemistry Association (IUPAC, study above).
The results are shown in Table 3.
aA−T=アルファ−トコフェロール; B−T=ベータ−トコフェロール; G−T=ガンマ−トコフェロール; D−T=デルタ−トコフェロール
b初期濃度(0)および上記条件で加熱25時間後に得られた濃度(25)を示す。
a AT = alpha-tocopherol; BT = beta-tocopherol; GT = gamma-tocopherol; DT = delta-tocopherol
b Initial concentration (0) and concentration (25) obtained after 25 hours of heating under the above conditions are shown.
Claims (35)
a)F1種子を得るために、NP−40植物とBSD−2−423植物の間で制御交雑を行うこと、
b)F2種子を得るために、F1種子から得られるF1植物を自家受精させること、
c)油中に存在する全脂肪酸の15%より多い高パルミチン酸含量と、油中に存在する全脂肪酸の45%より多い高オレイン酸含量との組合せを有するF2種子を選択すること、
d)F2植物のF3種子を産生させること、
e)前記F3種子由来の植物とT2100植物の間で制御交雑を行うこと、
f)F2種子を得るために、この交雑からのF1種子から得られるF1植物を自家受精させること、
g)全脂肪酸の15%より多い高パルミチン酸含量と、油中に存在する全脂肪酸の45%より多い高オレイン酸含量と、種子中の全トコフェロールの85%より多い高ガンマ−トコフェロール含量の組合せを有するF2種子を選択すること、
h)F2植物のF3種子を産生させること、
i)飽和脂肪酸(パルミチン酸およびステアリン酸)含量が油中に存在する全脂肪酸の15〜45%であり、オレイン酸含量が油中に存在する全脂肪酸の45〜75%であり、ガンマ−トコフェロールおよびデルタ−トコフェロールの合計含量が油中に存在する全トコフェロールの85%よりも多い、F3種子を選択すること、および
j)F3種子から油を抽出すること、を含む方法により得られる、該ヒマワリ油。 Saturated fatty acids (palmitic acid and stearic acid) content is 15-45% of the total fatty acids present in the oil, oleic acid content is 45-75% of the total fatty acids present in the oil, gamma-tocopherol and delta A highly heat-stable sunflower oil extracted from sunflower seeds, wherein the total content of tocopherol is greater than 85% of the total tocopherols present in the oil ,
a) performing a controlled cross between NP-40 and BSD-2-423 plants to obtain F1 seeds;
b) self-fertilizing F1 plants obtained from F1 seeds to obtain F2 seeds;
c) selecting F2 seeds having a combination of a high palmitic acid content of greater than 15% of the total fatty acids present in the oil and a high oleic acid content of greater than 45% of the total fatty acids present in the oil;
d) producing F3 seeds of F2 plants;
e) performing a controlled cross between the F3 seed-derived plant and the T2100 plant;
f) self-fertilizing F1 plants obtained from F1 seeds from this cross to obtain F2 seeds;
g) A combination of a high palmitic acid content of more than 15% of the total fatty acids, a high oleic acid content of more than 45% of the total fatty acids present in the oil and a high gamma-tocopherol content of more than 85% of the total tocopherols in the seeds. Selecting F2 seeds having
h) producing F3 seeds of F2 plants;
i) gamma-tocopherol with a saturated fatty acid (palmitic acid and stearic acid) content of 15-45% of the total fatty acids present in the oil and an oleic acid content of 45-75% of the total fatty acids present in the oil; And selecting F3 seeds, wherein the total content of delta-tocopherol is greater than 85% of the total tocopherols present in the oil; and
j) The sunflower oil obtained by a method comprising extracting oil from F3 seeds .
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JP5704922B2 true JP5704922B2 (en) | 2015-04-22 |
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JP2010538804A Active JP5704922B2 (en) | 2007-12-21 | 2008-11-27 | Sunflower oil with high heat stability |
JP2014247259A Active JP6192058B2 (en) | 2007-12-21 | 2014-12-05 | Sunflower oil with high heat stability |
JP2017111637A Pending JP2018009151A (en) | 2007-12-21 | 2017-06-06 | Sunflower oil high in heat stability |
JP2019021732A Active JP7217164B2 (en) | 2007-12-21 | 2019-02-08 | Sunflower oil with high heat stability |
JP2021065427A Active JP7213908B2 (en) | 2007-12-21 | 2021-04-07 | Sunflower oil with high heat stability |
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JP2014247259A Active JP6192058B2 (en) | 2007-12-21 | 2014-12-05 | Sunflower oil with high heat stability |
JP2017111637A Pending JP2018009151A (en) | 2007-12-21 | 2017-06-06 | Sunflower oil high in heat stability |
JP2019021732A Active JP7217164B2 (en) | 2007-12-21 | 2019-02-08 | Sunflower oil with high heat stability |
JP2021065427A Active JP7213908B2 (en) | 2007-12-21 | 2021-04-07 | Sunflower oil with high heat stability |
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US (1) | US9375023B2 (en) |
EP (1) | EP2243379B1 (en) |
JP (5) | JP5704922B2 (en) |
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CN (1) | CN101917864A (en) |
BR (1) | BRPI0821333B1 (en) |
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SI (1) | SI2243379T1 (en) |
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JP2019090054A (en) * | 2007-12-21 | 2019-06-13 | コンセホ・スペリオール・デ・インベスティガシオネス・シエンティフィカス(シーエスアイシー)Consejo Superior De Investigaciones Cientificas | Sunflower oil having high heat stability |
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FR2975702B1 (en) * | 2011-05-25 | 2013-05-10 | Arkema France | REACTIVE TRACTION PROCESS DIRECTLY ON A FAT PIE |
CN102239933B (en) * | 2011-06-23 | 2013-05-15 | 中国农业科学院油料作物研究所 | Family balance formula oil and preparation method thereof |
CN106578136A (en) * | 2016-11-11 | 2017-04-26 | 南海油脂工业(赤湾)有限公司 | Frying resistant edible vegetable oil and preparation and application thereof |
KR20200062741A (en) | 2018-11-27 | 2020-06-04 | 박영길 | Cradle device having cradle pillar disposed on oblique line |
WO2024011043A1 (en) * | 2022-07-06 | 2024-01-11 | Cargill, Incorporated | Nutritional composition |
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MX9603046A (en) * | 1994-01-31 | 1998-05-31 | Consejo Superior Investigacion | Sunflower seeds and oil having a high stearic acid content. |
US5710366A (en) * | 1995-06-07 | 1998-01-20 | Pioneer Hi-Bred International, Inc. | Helianthus annuus bearing an endogenous oil wherein the levels of palmitic acid and oleic acid are provided in an atypical combination via genetic control |
DK0965631T3 (en) | 1998-06-05 | 2013-07-22 | Consejo Superior Investigacion | Highly stable plant oils |
US6388113B1 (en) * | 1999-06-04 | 2002-05-14 | Consejo Superior De Investigaciones Cientificas ( Csic) | High oleic/high stearic sunflower oils |
US6348610B1 (en) | 1999-06-04 | 2002-02-19 | Consejo Superior De Investigaciones Cientificas (Csic) | Oil from seeds with a modified fatty acid composition |
AU783474B2 (en) * | 1999-06-04 | 2005-10-27 | Consejo Superior De Investigaciones Cientificas | Use of high oleic high stearic oils |
ES2233174B1 (en) * | 2003-04-10 | 2006-10-01 | Consejo Sup. Investig. Cientificas | SUNFLOWER SEED OIL WITH HIGH CONTENT IN DELTA-TOCOFEROL. |
UA92455C2 (en) | 2003-11-14 | 2010-11-10 | Консехо Супериор Де Инвестигасионес Сьентификас | Sunflower oil, seeds and plants with modified fatty acid distribution in the triacylglycerol molecule |
ES2325516B1 (en) * | 2007-12-21 | 2010-06-17 | Consejo Superior De Investigaciones Cientificas | SUNFLOWER OIL WITH HIGH THERMOSTABILITY. |
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JP2019090054A (en) * | 2007-12-21 | 2019-06-13 | コンセホ・スペリオール・デ・インベスティガシオネス・シエンティフィカス(シーエスアイシー)Consejo Superior De Investigaciones Cientificas | Sunflower oil having high heat stability |
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